The oldest lighthouse in the world, the Pharos of Alexandria, had one job: mark the entrance to the harbor. Tell ships that the port is here. You've arrived. This is where you come in.
That's what a lighthouse has always done. It doesn't steer your ship. It doesn't tell you what to do. When everything around you is dark, unfamiliar, and uncertain, it sends one steady signal: the harbor is here. You're not lost. Keep coming.
Most founders who are serious about selling can point to a moment. Something shifted. Maybe it's a quiet moment on a walk. Maybe it's a conversation that won't leave you alone. Maybe it's a feeling you can't explain to anyone around you. But something cuts through the noise and says: it's time. Pay attention.
That moment doesn't make the decision for you. It just tells you the harbor exists.
But knowing the harbor exists and navigating the channel are two different things. The waters near the harbor are the most dangerous stretch of the entire voyage. Shallow channels. Hidden sandbars. Shifting currents. Tight passages that only someone who knows these specific waters can navigate safely. This is where ships run aground. Not in the middle of the ocean, but in the last few miles before safety.
So a harbor pilot boards the vessel. He climbs up while the ship is still moving and stands alongside the captain through the most dangerous stretch. The captain never leaves the helm. But now he has someone beside him who knows these specific waters. A steady voice. Someone who knows where the sandbars are.
Waypoint is both. The signal that tells you the harbor exists. And the steady hand beside you through the channel.
My name is Jonathan Sherrill. I started working in my family's business at fourteen. By my early thirties I was running the company... five locations, over a hundred employees. Then I was let go at thirty-four from the only job I'd ever had. Three-year noncompete. The only industry I knew.
I built Quicken Steel from scratch after that. My father was my financial partner. We started with one employee in a shuttered sawmill and grew it into something real. I'd already helped sell my father's previous company, so I understood the mechanics of a deal. When it came time to sell Quicken Steel, my exit was clean. No earn-out. No equity left in the business. I walked away completely.
I was more prepared than most. And I was still blindsided by what happened to me personally on the other side. Not because I got the deal wrong. Because nobody in the entire industry is focused on the person going through it.
I've spent most of my adult life studying what it takes to lead well and leave well. Not just M&A strategy and deal mechanics, but the deeper work... wisdom, formation, what it actually means to steward a life and not just a business. That's what I bring to this room.
After I sold, I started having conversations with other founders who had been through it or were heading into it. I'd ask one question nobody in the exit industry ever asks: how are you doing? And I kept hearing the same thing. Nobody had prepared them for how big this actually is. Not just the deal. Everything around it.
After co-authoring The Extraordinary Exit with Andy Harris, I started to see the full picture. The exit journey is littered with decisions, risks, and emotional weight that nobody talks about honestly. There are plenty of people who help with the deal. Nobody was walking with the founder through the whole passage. The practical complexity. The personal toll. The stuff that keeps you up at night before the sale and hits you at 10 AM on a Tuesday after it.
And with the right room, the right process, and the right people beside you, you don't have to figure it out alone. That's why Waypoint exists.
Masterminds help you build.
Waypoint helps you land.
WAYPOINT
Clarity and direction for founders in transition.
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